How to Deliver Bad News and Insights for CEO Relationships

Nobody prepared me for the hardest part of being a manager: delivering bad news and somehow maintaining trust while doing it. After two decades in product development and six years of executive leadership, I’ve learned that our industry’s rapid growth has created a generation of smart, capable leaders who are completely unprepared for these emotionally charged moments. Whether you’re telling an employee they’re underperforming, informing customers about a delay, or pushing back on your boss’s unrealistic timeline, these conversations can make or break your credibility as a leader.

What You’ll Learn
· The three critical scenarios every manager faces — How to navigate difficult conversations with employees, customers, and your boss using proven frameworks that preserve relationships while addressing real problems

· A systematic approach to employee performance issues — Learn to detect early warning signs, prepare with specific written plans, and deliver feedback that gives people a clear path forward instead of leaving them confused or defensive

· Customer communication strategies that build trust — Master the art of transparency, empathy, and accountability when things go wrong, including how to close the loop and rebuild damaged relationships

· The nuanced art of managing up — Understand the difference between adaptive and technical feedback, use “peace time” for micro-feedback, and develop backup plans when challenging your boss’s decisions

· Bonus: Executive-level insights for CEO relationships — Practical strategies for engaging with senior leadership without starting from a defensive position, drawn from real C-suite experience

Speaker Bio:
Mahesh Guruswamy is the Chief Product and Technology Officer at Kickstarter and author of “How to Deliver Bad News and Get Away With It.” With over 20 years in software development and more than a decade as a people manager, he has navigated the messy realities of leadership at companies like Amazon, Smartsheet, Kajabi, and Mosaic. Known for his “calm but oddly ambitious” approach, Mahesh specializes in helping emerging product development leaders tackle the emotional and practical challenges that no one warns you about in management. His authentic, systems-oriented guidance draws from real failures and hard-won lessons, making him a trusted mentor for managers facing the inevitable difficult conversations that define leadership careers.”